5-(5-nitro-2-furyl)-1,3,4-oxadiazoline-2-one or thione and process



United States Patent O S-(S-NITRO-Z-FURYL)-1,3,4-OXADIAZOL[NE-2- ONE OR THIONE AND PROCESS William R. Sherman, Waukegan, Ill., assignor to Abbott Laboratories, North Chicago, 111., a corporation of Illinois No Drawing. Application October '30, 1958 Serial No. 770,598

6 Claims. (Cl. 260307) This invention relates to novel chemical compounds having the formula:

CH-CH OzN-il ICI- wherein X represents oxygen or sulfur. These new compounds are crystalline solids somewhat soluble in many organic solvents and of very low solubility in water. They have been found to be active as parasiticides and, particularly, as coccidiostats and antibacterial agents. They are adapted to be employed as active toxic constituents of disinfectant compositions for the control of microorganisms such as Micrococcus pyogenes var. aureus, Salmonella typhimurium and Escherichia call. For such use, the compounds may be dispersed on an inert, finely divided solid and employed as a dust. Alternatively, they may be dispersed in water and employed as a spray. The products may likewise be employed as constituents of oil and water emulsions with or without a wetting, dispersing or emulsifying agent. In representative operations, 5- (5 nitro 2 furyl) 1,3,4 oxadiazoline 2 one gave complete inhibition of the growth of Micrococcus pyogenes var. aureus, Salmonella typhimurium, Proteus vulgaris, Proteus mirabilis and Escherichia coli when employed as an aqueous composition containing 50 parts by weight of said compound per million parts by weight of ultimate mixture.

The new compounds may be prepared by the reaction of phosgene or thiophosgene with 5-nitro-2-furoylhydrazide having the formula:

CHCH

The reaction is carried out in the presence of an inert solvent such as dilute aqueous hydrochloric acid or dioxane. Good results are obtained when employing substantially equimolar proportions of the reactants. The reaction takes place smoothly at temperatures of from C. to 80 C. with the formation of the desired product and hydrogen chloride of reaction. Upon completion of the reaction, the desired product may be separated in conventional fashion.

In carrying out th reaction, -nitro-2-furoylhydr-azide dissolved in the reaction solvent is reacted with phosgene or thiophosgene by introducing phosgene gas or liquid thiophosgene beneath the surface of the liquid reaction mixture. The reaction is carried out with stirring and at a temperature of from 0 C. to 80 C. The desired product which precipitates as a solid during the reaction EXAMPLE I 5-(5-nitr0-2-furyl) -1,3,4-0xadiaz0Zi'ne-Z-one CH-CH O OaN-C il-o c=0 5-nitro-2 furoylhydrazide (50.15 grams, 0.30 mole) was dissolved in 500 milliliters of a dilute aqueous solution of hydrochloric acid containing one part of concentrated hydrochloric acid and ten parts of water. The resulting solution was cooled to a temperature of 10 C. and phosgene gas introduced beneath the surface of the liquid reaction mixture with constant stirring for a period of one hour. The solid product which formed during the reaction was separated by filtration. Upon crystallization from an acetone-water mixture, there was obtained a 5-(5-nitro-2-furyl) -l,3,4-oxadiazoline-2one product as a crystalline, cream-colored solid which melted at 201202 C. with decomposition. This product contained 36.36 percent carbon, 1.80 percent hydrogen and 40.36 percent oxygen compared to the calculated values of 36.56 percent, 1.52 percent and 40.59 percent, respectively.

EXAMPLE II 5 (5 -nitro-2-furyl -1 ,3 ,4 -0xadiazoline-2 -th ione CH-CH O2N( i H I claim: 1. A compound having the formula:

OHCH 0 O2N- lC \C=X ll lH wherein X represents a member of of oxygen and sulfur.

2. 5-(5-nitro-2-furyl)-1,3 ,4-oxadiazoline-2-one.

3. 5-(5-nitro-2-furyl)-1,3,4-oxadiazoline-2-thione.

4. A method for the manufacture of a compound having the formula:

the group consisting:

wherein X represents a member of the group consisting y M v 2,918,478 3 4 of oxygen and sulfur which comprises reacting S-nitro- 6. A method for the manufacture of S-(S-nitro-Z Z-furoylhydrazide with a member of the group consistfuryD-l,3,4-oxadiazoline-2-thione which comprises reacting of phosgene and thiophosgene. ing equimolar quantities of S-nitro-2-furoylhydrazide and 5. A method for the manufacture of 5-(5-nitro-2-furyl)- thiophosgene at a t perature of from 0 to 80 C. and

1,3,4-oxadiazoline-2-one which comprises reacting equi- 5 recovering the resultant product. molar quantities of S-nitro-Z-furoylhydrazide and phosgene at a temperature of from 0 to 80 C. and recov- References Cted m the fi of thls Patent ering the resultant product. Yale et al.: Chem. Abstracts, vol. 49, col. 3964 (1955). 

1. A COMPOUND HAVING THE FORMULA: 